The Chronicle has launched a new weekly Travel newsletter! Sign up here.

Unlike planning car trips, where enormous green highway signs point the way and online mapping is nearly foolproof, plotting the best route for a long bike trip requires a little digging. But once you get the hang of it, planning can become as appealing as the actual ride.

Having planned at least two dozen bike trips in the past 10 years, I find myself in idle moments plotting new routes on Google Maps and daydreaming about climbs, descents and scenery.

Here are the five key areas you should be thinking about for an awesome and successful bike expedition.

In California, a few general climate principles can help you get started planning your first bike trip. I try to avoid extreme heat and cold. Since there is always pleasant weather somewhere in California, with a little advance planning, you can pick the right trip for the time of year.

In the first few months of the year, the lowlands and valleys (below 2,000 feet in elevation) are green and lush, with highs in the 50s and 60s. By spring, the foothills (2,000-4,000 feet) offer pleasant temperatures in the 60s and 70s. In the summer, previously snowbound mountain passes above 6,000 feet finally open and provide refuge from the worst summer heat. For example, after the wet winter of 2017, I biked through Lassen Volcanic National Park at the end of July, when the road over the 8,850-foot summit had been cleared of snow only days before, and the temperature was perfect.

The general rule is that the closer to summer your ride is, the higher your elevation should be. (“California Dream Riding,” a classic bike book by the legendary Northern California cyclist Chuck “Bodfish” Elliot, is organized this way.) Go to www.weather.com and click the “Monthly” tab for information on average monthly temperatures and precipitation.

2. Wind

Along with sailors, surfers, meteorologists and farmers, bicyclists are among the various subcultures who obsess over wind patterns. My wife and I have a saying: When the wind ain’t your friend, nobody’s your friend. Biking up a steep hill can be tough but rewarding; riding into a persistent headwind is simply demoralizing.

In summer in Northern California, for example, the prevailing winds blow from the north on the coast and from the south inland. Winds from the west predominate all over California. For our summer trip, we planned a counterclockwise loop, from Davis to Mount Shasta and back down to Santa Rosa, in order to keep the wind in our favor both northbound and southbound. If you must ride against the prevailing wind, start early: Wind tends to pick up over the day and peak in late afternoon. For up-to-date wind reports, check out www.windmapper.com.

3. Mapping and terrain

Once you’ve got a few key places and areas to visit in mind, it’s time to think about mapping your trip.

Route-planning sites like www.ridewithgps.com let you create your own maps and transfer them easily to your phone or bike computer. These sites automatically create mile-by-mile elevation profiles, including the grade of each hill. You’ll need to know: 3 percent is a noticeable incline; 7 percent is a tough hill; anything in the double digits is a ticket to what cyclists call “the pain cave” and should not be attempted lightly. A rule of thumb is that if a ride has more than 100 feet of climbing per mile, it will be tough on quads and calves.

Use Google Street View to scout your trip virtually before you take it for real. It’ll give you a good preview of scenery, traffic, pavement quality and, for busy roads, bike lanes or shoulders. Street View also helps you ensure that a line on the map is a real road open to the public and not one of the phantom roads that bedevil even high-quality paper and online maps.

If you’re still not sure about whether a particular route is bikeable, try querying at www.bikeforums.net or Reddit’s Bay Area cycling community: www.reddit.com/r/BAbike. “Can I bike here?” is a popular message to ask people on Reddit, and if a route is even remotely rideable, some fellow cyclist will write back assuring you they’ve done it.

4. Services and supplies

Next, think about what supplies and services you’ll need and where they can be had on your route. Make sure there are places to stay (or camp, if you’re into that) at reasonable intervals, and places to fill up on food and water.

Being able to cover a lot of ground in a day is one of the great attractions of bike travel, but there are stretches of rural California with no services for 50 to 100 miles. For instance, a trip my wife and I took last summer featured a 55-mile stretch in rural Siskiyou County where there were no supplies. For small towns that have only one restaurant or general store, call ahead to confirm they’ll be open when you’re passing through. Churches, fire stations and schools sometimes have water spigots outside in the absence of businesses. All these considerations mean you’ll likely end up tweaking your route as you plan the trip: Keep refining it until everything lines up.

5. Must-have gear

We won’t bore you with our full packing list, but here are some things we only started bringing after learning the hard way:

Pocket knife: Use this to slice food and pick bits of glass out of your tires.

Duct tape and zip ties: For fixing minor issues, like holes in your travel bags or loose water bottle cages.

Extra plastic bags: For holding laundry or snacks. If you get caught in a rainstorm, put them between your socks and shoes for some instant waterproofing.

Bicycle multi-tool: This is the rider’s Swiss army knife. It has hex wrenches, screwdrivers and chain tools.

Inevitably, there will be some item you forget, some route detail that doesn’t work out as planned. A good plan will set you out right, but an openness to what the ride throws at you is just as important as anything listed here.

Lily Janiak joined the San Francisco Chronicle as theater critic in May 2016. Previously, her writing appeared in Theatre Bay Area, American Theatre, SF Weekly, the Village Voice and HowlRound. She holds a BA in theater studies from Yale and an MA in drama from San Francisco State.